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Vasorelaxant activity of 7-β-O-glycosides biosynthesized from flavonoids.
Eur J Pharmacol. 2014 Jun 15; 733:75-80.EJ

Abstract

In this work we report the vasorelaxant activity of 7-β-O-glycosides obtained with biosynthesis of naringenin-7-β-O-glycoside (3) and quercetin-7-β-O-glycoside (4). These compounds were obtained from naringenin (1) and quercetin (2) glycosylation catalyzed by Beauveria bassiana ATCC 7159. Screening of the best strain as a catalyst for glycosylation was carried out and the reaction conditions established. Cultures were grown in PDSM medium for 7 days at 27 °C. After purification by reverse-phase preparative HPLC, naringenin-7-β-O-glycoside (3) and quercetin-7-β-O-glycoside (4) were identified by (1)H and (13)C NMR. The right position and β-configuration of the glucose was determined through HSQC and HMBC experiments. The vasorelaxation potential of naringenin, quercetin and its glycosylated derivatives was evaluated using isolated aorta in vitro models. Interestingly, results suggest that vasorelaxation properties of naringenin, rutin and its glycosides are due to different pathways.

Authors+Show Affiliations

Laboratório de Bioconversão, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil.Laboratório de Bioconversão, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil.Laboratório de Bioconversão, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil.Laboratório de Farmacologia Cardiovascular, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil.Laboratório de Farmacologia Cardiovascular, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil.Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Campus Samambaia, CEP: 74.001-970, Goiânia, GO, Brazil.Laboratório de Farmacologia Cardiovascular, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil.Laboratório de Bioconversão, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil. Electronic address: valeriaoliveira@ufg.br.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24704375

Citation

Penso, Juliana, et al. "Vasorelaxant Activity of 7-β-O-glycosides Biosynthesized From Flavonoids." European Journal of Pharmacology, vol. 733, 2014, pp. 75-80.
Penso J, Cordeiro KC, da Cunha CR, et al. Vasorelaxant activity of 7-β-O-glycosides biosynthesized from flavonoids. Eur J Pharmacol. 2014;733:75-80.
Penso, J., Cordeiro, K. C., da Cunha, C. R., da Silva Castro, P. F., Martins, D. R., Lião, L. M., Rocha, M. L., & de Oliveira, V. (2014). Vasorelaxant activity of 7-β-O-glycosides biosynthesized from flavonoids. European Journal of Pharmacology, 733, 75-80. https://doi.org/10.1016/j.ejphar.2014.03.014
Penso J, et al. Vasorelaxant Activity of 7-β-O-glycosides Biosynthesized From Flavonoids. Eur J Pharmacol. 2014 Jun 15;733:75-80. PubMed PMID: 24704375.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Vasorelaxant activity of 7-β-O-glycosides biosynthesized from flavonoids. AU - Penso,Juliana, AU - Cordeiro,Kelly C F A, AU - da Cunha,Carla R M, AU - da Silva Castro,Patricia F, AU - Martins,Daniella R, AU - Lião,Luciano M, AU - Rocha,Matheus L, AU - de Oliveira,Valéria, Y1 - 2014/04/01/ PY - 2013/10/09/received PY - 2014/03/06/revised PY - 2014/03/10/accepted PY - 2014/4/8/entrez PY - 2014/4/8/pubmed PY - 2015/1/6/medline KW - Aorta relaxation KW - Beauveria bassiana KW - Glycosylation KW - Naringenin KW - Quercetin SP - 75 EP - 80 JF - European journal of pharmacology JO - Eur. J. Pharmacol. VL - 733 N2 - In this work we report the vasorelaxant activity of 7-β-O-glycosides obtained with biosynthesis of naringenin-7-β-O-glycoside (3) and quercetin-7-β-O-glycoside (4). These compounds were obtained from naringenin (1) and quercetin (2) glycosylation catalyzed by Beauveria bassiana ATCC 7159. Screening of the best strain as a catalyst for glycosylation was carried out and the reaction conditions established. Cultures were grown in PDSM medium for 7 days at 27 °C. After purification by reverse-phase preparative HPLC, naringenin-7-β-O-glycoside (3) and quercetin-7-β-O-glycoside (4) were identified by (1)H and (13)C NMR. The right position and β-configuration of the glucose was determined through HSQC and HMBC experiments. The vasorelaxation potential of naringenin, quercetin and its glycosylated derivatives was evaluated using isolated aorta in vitro models. Interestingly, results suggest that vasorelaxation properties of naringenin, rutin and its glycosides are due to different pathways. SN - 1879-0712 UR - https://www.unboundmedicine.com/medline/citation/24704375/Vasorelaxant_activity_of_7_β_O_glycosides_biosynthesized_from_flavonoids_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0014-2999(14)00197-6 DB - PRIME DP - Unbound Medicine ER -